Sam and Dean were at the grocery store stocking up on pie. 2 years worth to be exact. On their way to the pastry section they passed the produce buckets. Dean nearly fainted (but in a manly way). The glistening golden dandelion unicorn colored fruit lay there, more seductive than Nicholas Cage's eyebrows, beckoning him with a force more powerful than his man siren.
"Dean are you all right?!" shouted Sam.
"um... yeah... i'm..."
Dean got up and made his way to the banana bucket.
Just then Nicholas Cage swooped in wearing a bunny suit.
"I NEED THAT BANANA, IT'S THE KEY TO THE STATUE OF LIBERTY."
He stole the banana and flew out the window on his hovercraft.
Dean fell to the floor sobbing, and Sam, not knowing what to do now that he wasn't the one crying, called castiel.
Cas flew in wearing rainbow overalls.
"WTF are you wearing cas" said Sam while snapping his fingers in a Z formation.
"Sorry, I was just at woodstock playing the xlylaphonz with mozart"
"Dean's eyes are leaking"
"wut"
"idk i guess he has like feelingz or something"
"this moment calls for my angel stick!" said cas triumphantly putting his hands on his hips.
"ew cas, not here, please not here!" said Sam
"What?" said Cas, pulling out his silvery wand that angels stab each other with.
"oh, nvrmnd"
Sam watched as cas went over to dean with his angel stick in his hand... just then he realised
"Wait Cas! doesn't that thing make ppl ded?"
"only angels... and some koala bears; mostly those indigenous to southern australia... but not humans"
Cas poked dean with his stick and deans eyes drid right away.
"I've got to get back now," said cas "simon and garfunkel are coming on soon."
he pranced out the door in a whirl of sparkles and whipped cream. dean sat up.
"OMG WE HAVE TO GET THAT BANANA BACK"
"kay" said sam, and they leap frogged out to the impala.
"where are we going" said the impala
"TO THE STATUE OF LIBERTY" shouted dean
the impalas jet engines ignited and they were off.
about halfway to new york the impala asked why they were going to the statue of liberty.
"it's to rescue my one true love" replied dean casually
"wut"
"wut"
"wut"
"wut"
"wut"
"wut"
"wut"
"wut"
"wut"
"wut"
"wut"
"i thought i was your one true love" said the impala
"well i've moved on" said dean with a tone even douchier than size 12 crocs.
suddenly the impala stopped
"OUT!" she yelled
"what?" said sam and dean in unison
the impala pushed her eject button and sam and dean went flying out, they flew so far that they ended up in the 60s and as they were nearing the ground they saw that they were going to crash right into simon and garfunkel! They crashed onto the stage in the middle of their set and suddenly they were standing in front of a gajillion hippies.

"wait" said sam "those aren't hippies, those are just tie dye sheep!"
"well this wasn't what i was expecting woodstock to look like"
"yeah" said castiel, emerging from the sheep "the history books changed it to sound less lame than a radical sheep convention"
Everyone just sort of stood there staring at each other until simon and garfunkel were like
"hey man, um... we were kind of in the middle of a song."
"oh, sorry, we'll leave" said sam, blushing
"wait!" said dean "why don't we join you"
"ok" said simon and garfunkel shrugging
So they all sang a song and afterwords simon and garfunkel were like
"OMGF TAHT WAS SOOO GOOOD WE HAVE 2 START A BOYYY BAND!"
And from that day on they were known as "Simon, Garfunkel, and the Winchesters"

They were super popular (especially among the sheep demographic). Sam wrote a hit song called "real men do cry" and then dean wrote a hit song after that called "sam is a pussy (real men don't cry)" then sam wrote a song called "it's not a crime to have feelings" and dean wrote a song called "i liked you better with no soul" and then sam wrote a song called "it's not easy being the younger" and then dean wrote a song called "you're fucking with me, right?"
Soon after "you're fucking with me, right?" debewd as #1 on the music charts, simon and garfunkel decided that it was a bad idea for the winchesters to express themselves through music and also that they sang like miranda cosgrove, and it was really cramping their style. so they kicked the winchesters out of their band.